2-(Chloromethyl)-1H-imidazole hydrochloride → 2-[(2-Imidazoline-2-ylmethyl)thio]-1H-naphth[2,3-d]imidazoldihydrochloride

HRID 1413113Notes

Reaction equation

HRID 1413113 reaction equation
[NH:1]1[C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][C:4]=2[N:3]=[C:2]1[SH:14])[CH:11]=[CH:10][CH:9]=[CH:8]3.[ClH:15].[Cl:16][CH2:17][C:18]1[NH:19][CH:20]=[CH:21][N:22]=1>CN(C)C=O.C1(C)C=CC=CC=1>[ClH:16].[ClH:15].[NH:22]1[CH2:21][CH2:20][N:19]=[C:18]1[CH2:17][S:14][C:2]1[NH:3][C:4]2[CH:13]=[C:12]3[C:7](=[CH:6][C:5]=2[N:1]=1)[CH:8]=[CH:9][CH:10]=[CH:11]3

Participants

5

Reactant 2

HCID 27609292-(Chloromethyl)-1H-imidazole hydrochlorideHCID 1785277551H-benzo[f]benzimidazole-2-thiol

Product 1

HCID 705692132-[(2-Imidazoline-2-ylmethyl)thio]-1H-naphth[2,3-d]imidazoldihydrochlorideYield 58.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

10.0 g 1H-Naphth[2,3-d]imidazole-2-thiol and 8.0 g of 2-chloromethylimidazole-hydrochloride were heated for 3 hours at 90° in 50 ml of dimethylformamide. The reaction mixture was cooled to room temperature and then diluted with 200 ml of toluene. The residue was suction filtered, washed well with toluene, and crystallized from 700 ml of methanol, with the addition of 300 ml of ether. 10.3 g of 2-[(2-Imidazoline-2-ylmethyl)thio]-1H-naphth[2,3-d]imidazoldihydrochloride having an m.p. of 227°-228° were obtained.

Workup

  1. filtrationfiltered
  2. washwashed well with toluene
  3. customcrystallized from 700 ml of methanol, with the addition of 300 ml of ether

Sources & evidence

ORD record
ord-29872955b0284e9e861e4e0a704ba025
Source dataset
uspto-grants-1981_02
Patent number
US04248880

Reaction notes

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